Tetrabutylammonium Fluoride → HCID 67436478, compound

HRID 1968887Notes

Reaction equation

HRID 1968887 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][C@H:8]([CH2:13][N:14]([C:27]1[CH:32]=[CH:31][C:30]([O:33][Si](C(C)(C)C)(C)C)=[CH:29][CH:28]=1)[C:15]([C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1)=[O:16])[C@@H:9]([CH3:12])[CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6](=[O:41])[NH:7][C@H:8]([CH2:13][N:14]([C:15]([C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1)=[O:16])[C:27]1[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=1)[C@@H:9]([CH3:12])[CH2:10][CH3:11])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67437172HCID 67437172, compound

Product 1

HCID 67436478HCID 67436478, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [(1S,2S)-1-({[4-(t-butyl-dimethyl-silanyloxy)-phenyl]-[(1R,2R)-2-(5-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-amino}-methyl)-2-methyl-butyl]-carbamic acid tert-butyl ester (190 mg) in THF (3 mL) was added TBAF in THF (1M, 1 mL) the resulting solution was stirred at rt for 2 h. The reaction mixture was diluted with EtOAc (30 mL) and washed with H2O (2×15 mL) and brine (15 mL). The EtOAc layer was dried (Na2SO4) and concentrated to give the titled compound (102 mg). MS (MH+ 472).

Workup

  1. washwashed with H2O (2×15 mL) and brine (15 mL)
  2. dry with materialThe EtOAc layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2bc362975f6a4163b2531cf7998e7c4f
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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